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Amide directed C(sp3)-H functionalisation of saturated amines

Coomber, Charlotte E.; (2019) Amide directed C(sp3)-H functionalisation of saturated amines. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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This thesis describes research towards the development of C-H activation reactions of saturated amines. // Chapter 1 describes current approaches towards directed C-H activation. // Chapter 2 covers approaches towards the amide directed C-H functionalisation of saturated amines. Methodology for the arylation of bicyclic amines is developed, which gives high yields of arylated products with a variety of aryl iodides and bromides. The methodology is applied to mono-, bi- and tricyclic amines with excellent yields. The reaction is improved by the introduction of a novel solvent for C-H activation, and allows for the arylation of more challenging amine substrates. It is also shown that a simple methyl substitution on the directing group can improve the yield of arylated products. // Chapter 3 investigates how the directing group employed can influence both the selectivity and yields of C-H functionalisation. Different directing groups are investigated on a range of amines to establish if they can improve yield and selectivity. // Chapter 4 describes efforts towards elucidating the mechanism for C-H activation. Plausible reaction intermediates are isolated. Reaction progress kinetic analysis is performed to further probe the reaction and to establish the rate dependence on the different reaction components. Same excess experiments are employed to establish the effect of the product on catalyst activity and also to determine if there is any catalyst degradation over the course of the reaction. // Chapter 5 describes efforts towards sustainable amide synthesis. Direct condensation of a carboxylic acid with an amine using a borate catalyst is employed. Existing methods developed within the group are expanded to improve yields for more polar substrates, and poorly nucleophilic amines. A new ester solvent is introduced to improve solubility of these substrates and improve the sustainability and reduce cost of the process.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Amide directed C(sp3)-H functionalisation of saturated amines
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Copyright © The Author 2019. Original content in this thesis is licensed under the terms of the Creative Commons Attribution 4.0 International (CC BY 4.0) Licence (https://creativecommons.org/licenses/by/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10082394
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